Guilford Homes for Sale

Welcome to Guilford, Vermont – a hidden gem nestled in the picturesque Windham County. Known for its stunning natural beauty and tight-knit community, Guilford is where charming New England landscapes meet a vibrant local culture. With rolling hills, lush forests, and serene waterways, this quaint town offers a peaceful retreat for those seeking a slower pace of life.

Guilford is steeped in history, with roots dating back to the late 18th century. Today, it boasts a rich tapestry of community events, local farmers' markets, and artisanal shops that reflect the spirit of its residents. The town is also conveniently located near the lively town of Brattleboro, providing easy access to shopping, dining, and entertainment options.

For those considering a move to this idyllic area, there are a variety of homes for sale that cater to different lifestyles and preferences. Whether you’re looking for a cozy cottage surrounded by nature, a spacious family home with modern amenities, or a charming farmhouse full of character, Guilford has something for everyone. Many properties feature breathtaking views, expansive yards, and proximity to outdoor recreational activities such as hiking, fishing, and skiing.

Investing in a home in Guilford means embracing a lifestyle rich in community and nature. With its friendly atmosphere, excellent schools, and a strong sense of belonging, Guilford is not just a place to live – it’s a place to thrive. Explore the available homes for sale today and discover how you can become part of this enchanting Vermont community!

Newest Guilford Homes for Sale

$289,000

2 Beds ⋅ 1 Baths ⋅ 5106522 MLS

Tucked into a peaceful, wooded setting on 2.1 acres in Guilford, just over the Massachusetts border, this cozy 2-bedroom, 1-bath home offers simple Vermont living with plenty of charm. Designed for convenient one-level living, the home features a back deck overlooking the yard surrounded by the quiet of the woods. Several recent improvements add to the home’s comfort and practicality, including a re-shingled roof in 2023, a 50-amp exterior generator connection, and new water and electric lines for a washer and dryer in a bedroom closet. The home is heated by a new woodstove installed in July 2026, with electric baseboard heat providing added flexibility. The property is also close to Sweet Pond State Park, a peaceful local favorite offering a scenic woodland trail, along with opportunities for paddling, swimming, and enjoying the outdoors. Rustic and comfortable, this Vermont property could make a wonderful year-round home, weekend getaway, or downsizing option for someone looking for a smaller place surrounded by nature. Enjoy mornings on the back deck listening to the birds, space to garden or relax outdoors, and the simplicity of having your own little retreat in the Guilford woods.

45 Kopkind Rd, Guilford

$275,000

5106167 MLS

A perfect start! Well, power and driveway are all installed & septic design is available. The building constructed on slab, mostly finished surfaces, cathedral ceiling in the "living room". The interior is already sectioned into 4 rooms, waiting for kitchen and bath fixtures. Seller has plans for a one or 2 unit home build out. Sitting near the end of a quiet country road in no zoning Guilford, minutes to Brattleboro, interstate and shopping. Be snug as a bug by winter! Easy to show.

752 Butternut Rd, Guilford

$1,165,000

4 Beds ⋅ 3 Baths ⋅ 5104005 MLS

The Governor Carpenter Homestead, a pivotal piece of American history in Guilford, VT, is now accepting applications for its next Steward. This remarkable property was constructed in 1772 by Benjamin Carpenter, Vermont's first Lieutenant Governor. Lovingly maintained for decades, the residence combines historic integrity with modern functionality. Key features include: Architectural Significance: A gracious, charming house featuring a central chimney and a unique, squared-off Palladian window over the front door - one of only four known examples in Vermont. Historic Details: Five working fireplaces (including a large living room hearth with a beehive oven), and the original one-hole privy in the carriage house. Scenic Surroundings: Located across a dirt road from a lovely pond with remnants of an old barn foundation. Revolutionary Lore: An enclosed garden near the house is traditionally believed to have been a former campsite of Ethan Allen and the Green Mountain Boys. Modern Comfort: Features 21st-century plumbing while preserving its authentic character. New septic system installed in 2020. This is an unparalleled opportunity to own a property rich in history, charm, and character. A short drive to Brattleboro and everything it has to offer. Boston: 2.5 hrs. NYC 4 hrs. {Additional 30+/- acres available for an additional $250,000}

1472 Carpenter Hill Rd, Guilford

$235,000

4 Beds ⋅ 3 Baths ⋅ 5101087 MLS

Beautiful 1925 stucco Craftsman home needing TLC. Narrow strip oak flooring throughout, brick fireplace with original oak trim, original windows, beautiful oak staircase, arched doorways, dining room with enclosed porch, and a big country kitchen. There are many original features that make this property a great investment. The main house offers 2 sunny bedrooms; the adjacent finished apartment has another two. You could live in the apartment while you work on updating the house. You'll need to budget for insulating the walls, possible rewiring, renovating 2 bathrooms, plus cosmetics. If you have a business or need storage, there is a 24' x 34' barn with electricity and a large concrete parking lot. Once you see all that's here, you'll quickly realize your investment will yield a spacious and comfortable home with reliable income potential in a convenient Guilford location.

106 Coolidge Highway Unit 6-276, Guilford

$795,000

6 Beds ⋅ 7 Baths ⋅ 5093647 MLS

Only a fortunate few have the privilege of calling Green River Village home—a quintessential Vermont hamlet distinguished by its historic covered bridge, the 1811 timber crib dam, and the iconic wood-spired church proudly perched on the hillside above. Sited next to the bridge, the Green River Bridge House, originally a blacksmith shop, enjoys 300 feet of frontage along the Green River. Built in the 1830s and extensively renovated in 2002, the home overlooks a sweeping lawn that stretches to the river’s edge, framed by stone-walled perennial gardens and a private porch perfectly positioned to enjoy the beauty and tranquility of the surrounding landscape. The home is thoughtfully designed for rural family life centered around a welcoming country kitchen featuring a six-burner Garland stove, Moffat turbo oven, cozy wood stove, and an impressive marble-topped island ideal for casual dining and gathering. Friends are welcomed through the front door into a gracious living and dining room that is both elegant and inviting. Beyond, you'll find a bright and charming fireplaced pub for entertaining or quiet evenings, a cozy game room/office, and a sweeping staircase leading to the sleeping accommodations. Each bedroom is uniquely enchanting, featuring remarkable recessed chandeliers, dormer windows, and private en-suite baths, including one with a jetted tub for relaxing after a day of outdoor adventure. A lower-level office and studio apartment offer private exterior access with flexibility for personal or business use. Formerly, a bed and breakfast, this is an exceptional country retreat for family & friends. Skiing, cycling, hiking, swimming, fishing, kayaking, & endless exploration of Vermont’s scenic back roads are all at your door. Picture the gentle Green River lulling you asleep each night! Also listed under commercial MLS #5094262.

2435 Stage Rd, Guilford

$450,000

6 Beds ⋅ 3 Baths ⋅ 5093324 MLS

Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambiance and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of the home is a brick and stick built addition with an amazing green house room, built to bring the outdoors in and help warm the floor tiles for passive solar...great for plants or just soaking up the winter sun with a good book. Close the door between the 2 sides and create an in-law with full kitchen, bath and bedroom, all on one floor...for those who want to age in place. The land is a combination of open...for gardening and play and Vermont woods for nature hikes. Enjoy the fruit trees, perennials and plant some veggies for putting by...Private! But, off a paved road for easy access... Loved by the owners for many years, it is time to pass to the next generation who will bring upgrades and new ideas to this very special home.

4303 Hinesburg Rd, Guilford

$995,000

4 Beds ⋅ 4 Baths ⋅ 5092445 MLS

Surrounded by 65 acres of glorious land w/meadows, woodland, stone walls, and the meandering Keets Brook, this exceptional property offers a blend of beauty, privacy, and thoughtful design. The grounds are exquisitely landscaped with Gordon Hayward-designed gardens, specimen trees , stone walkways and mature blueberry bushes. A saltwater pool, private rear deck, oversized two-car garage, Kohler generator and sweet guest house w/bath & kitchenette complete this remarkable setting. The home (half new build and the other half totally renovated, all in 2001) is light-filled with imaginative touches that beautifully blend form and function. A front porch welcomes you into the mudroom featuring slate flooring, built-ins, closet, and adjacent laundry. The stunning kitchen is the centerpiece with maple and porcelain flooring, sloped ceilings, cherry cabinetry, slate countertops, huge windows framing the landscape, a Viking six-burner range, Sub-Zero refrigerator & Bosch dishwasher. To the right of the kitchen is a gracious dining room with oversized windows, cherry cabinetry w/slate counters, and a patio door to the deck and gardens. To the left is an intimate family room w/ a stained-glass window. A spacious living room offers hardwood flooring, fireplace with gas insert, and access to the front porch. The main level also includes a den with built-in cabinetry and a large bay window, along with a powder room and double closets. Upstairs (A/C) are 3 spacious bedrooms and a shared tile bath with double vanity and hand-painted dolphin tiles. The primary suite features cathedral ceilings with fan, a large window overlooking the gardens, walk-in closet, and a luxurious bath with jetted soaking tub surrounded by windows, double marble-top vanity, and a glass-fronted tile shower. A truly magical Vermont retreat where exceptional craftsmanship and breathtaking natural surroundings come together in perfect harmony. (Land is in Current Use for tax savings). Showings start 6/11/26.

3924 Sweet Pond Rd, Guilford

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